Episode 81 – Entrepreneurial You with Dorie Clark

‘You have to open yourself up… away from making money from something and understand that nowadays you make money because of something, and that’s a very different phenomenon.’

As a journalist, Dorie Clark used to make her living by writing content. But now she writes for free, and makes a much better living off the back of it. In this interview we explore the opportunities out there for anyone entrepreneurial enough to seize them, and the central role that writing and books play in this new world of attention and engagement.

Alison Jones: Hello and welcome to the Extraordinary Business Book Club. And this is very, very cool. I’m here today with Dorie Clark, who is a marketing strategy consultant, professional speaker, and author of Reinventing You and Standout, which was named the #1 leadership book of 2015 by Inc. Magazine, and one of the Top 10 Business Books of the Year by Forbes, which is very cool. She’s a former journalist, a film director, music producer, and presidential campaign spokeswoman, and the New York Times has described her as “an expert at self-reinvention and helping others make changes in their lives.” Her new book, just out, is Entrepreneurial You. Welcome to the show, Dorie.

Dorie Clark: Allison, thank you so much for having me. It’s great to chat.

Alison Jones: It’s really good to have you here. Now Lisa Earle McCloud recommended you as a guest for the show, and I can’t tell you how enthusiastic she was about having you on, so I’m expecting marvellous things from this conversation.

Dorie Clark: Well, thank you. All right. No pressure.

Alison Jones: No pressure, no. Now that is an extraordinary CV isn’t it? And I think running through everything you’ve done and everything you do now, I can see that single golden thread, take charge of who you are, take charge of what you do. Just tell me a little bit more about how you got here. How did that passion come about?

Dorie Clark: Oh, well thank you first of all. I appreciate it. Really in a lot of ways my entrepreneurial journey was accidental I guess like a lot of people’s. I originally thought I was going to be a journalist and I started out my first job after graduate school was as a political journalist and I ended up very rapidly, within a year of starting, getting laid off from my job and not being able to find another job in journalism so I had to adapt. That was kind of my first bout of reinvention and so I went to work on some political campaigns, which all ended up losing.

Alison Jones: It’s all going very well so far isn’t it?

Dorie Clark: Yeah, you know, my 20’s, I was just rocking it. Then finally I ended up running a nonprofit for a couple of years and as I was running a nonprofit what struck me at the time is kind of a surprising revelation, which is that running a nonprofit is exactly the same thing as running a business. It just suddenly hit me, “Wait, I could run my own business and I could probably have a lot less stress and I could probably make more money.” I thought, “Well, damn, why don’t I do that?” That was my kickstart into entrepreneurship which now is 11 years ago.

Alison Jones: It all came about because you got laid off that first time. It’s a real lesson in how resilience happens isn’t it?

Dorie Clark: Yeah, yeah. Absolutely.

Alison Jones: Oh, that’s really heartening. Tell us about Entrepreneurial You. What prompted you to write that? What problem, I always take to my clients, what problem are you solving? What problem does Entrepreneurial You solve for the people that you’ve written it for?

Dorie Clark: Well Alison, I decided that I would aim high and so Entrepreneurial You attempts to solve perhaps the biggest problem of all, which is how to make money.

Dorie Clark: Yes, thank you. Yeah, because my most recent book that I had written, Stand Out, which came out in 2015 was about a topic that I’m very passionate about and think is quite important, which is about how to become a recognised expert in your field. Of course that’s important. If you want to be able to charge what you’re worth you need to build up the respect of your peers. You need to be known in your industry. You want people coming to you and saying, “Oh yeah, you’ve got to work with her. She’s really good.” That’s important.

But what I came to realise in the course of giving talks and speaking to people about it is that there’s a lot of people out there who are very good at what they do. They are very accomplished. They have a lot to contribute and yet it is still very hard for them to earn a living doing what they’re good at. I wanted to create a book that really solved that problem in a lot of ways and so with Entrepreneurial You I went out and interviewed about 50 very successful six and seven and eight figure entrepreneurs to try to break down in great painstaking detail what is their business model, how specifically do they make money, and how can you create multiple income streams so that you can diversify and mitigate risk and also increase your opportunity to make even more money? I wrote a book to really try to be a roadmap for that.

Alison Jones: That’s fascinating and I can see that early journalistic background coming out there as well. That kind of curiosity. How is this working? Let me go and talk to some people.

Dorie Clark: Exactly. Exactly. When in doubt just talk to people who know more than you do.

Alison Jones: It’s a great, it’s a great mantra isn’t it? But you talked a lot about branding and I think this is such an interesting problem that you put your finger there because in a sense I think brand is a very overused word. I don’t think everybody actually has a brand if brand means what people think about you when you’re not there because frankly most people don’t think about us when we’re not there. That gap between how you get yourself front of mind and then how you monetize it I think is a real issue and it’s not often addressed actually.

Dorie Clark: Yeah, yeah. This is, Entrepreneurial You is a book that … Of course when you’re writing a book proposal you’re supposed to come up with a list of competitive works, et cetera, et cetera, but the honest truth is, I have not seen another book like this. This is really trying to go in depth with a topic that a lot of people steer away from. In our culture, money is talked about in very general terms. Like, “Yeah, it’s a great thing, earn more money,” blah, blah, blah.

But when it actually comes to details, like, “How much do people charge for this,” or, “No, no, specifically how do you make money,” people get a little dodgy and I wanted to try to break that down because I believe in transparency and I think that the more baggage there is around money, the less information people have, the worse off we are because we’re not able to fairly price our services. We don’t really know what is appropriate and that situation actually privileges the people who are already in power and who already have access to that inner coterie and that secret information.

If you were trying hard to make it and you’re not coming from a privileged place where you already know all the right people, if that information just isn’t publicly shared, you’re shut out of the discourse. And so I think this is really a way of levelling the playing field.

Alison Jones: And it’s also a really refreshing antidote to a lot of the guff, which is a technical British term, you maybe aware of or not, a lot of the guff that’s talked about, just follow your passion. That’s all very well but what does that look like when you’re trying to make money out of it?

Dorie Clark: That’s right.

Alison Jones: Yeah, it’s really refreshing. One of the things that people do, and it’s very much about putting themselves out there as an expert in their field and so on is create content and it’s something that I bang on about ad nauseum. It’s really really important for all businesses and you talk about, you really emphasise in everything you’ve done, the importance of creating, of sharing original content. Nobody pays you for that, right. How does that fit into your vision of the entrepreneur really making it work?

Dorie Clark: Well, you put your finger Alison on an interesting point, which I think is one of the key things that I explore in Entrepreneurial You, which is that in order for people to actually be savvy about earning money in the current economy, you have to do a little bit of extra thinking and extra digging. The people who adhere to the old models are going to be left behind.

To take an example from my own life, as a journalist of course I used to get paid to write articles. That was the definition of my job. But nowadays I spend plenty of time writing articles and yet I don’t get paid for it at all. It’s 20 years later. I have a lot more knowledge, a lot more experience, I get zero for it. If all I were doing was just bemoaning that state of affairs, I would probably be in pretty bad shape. I’d say, “Well, this thing I used to get money for, now I don’t so life is hard.”

But the truth is, there are other opportunities that are present, you just have to seize them. For instance, I actually make far more money now than I did when I was a journalist but the way that I have been able to do that is to monetize around the journalism. You write an article. Well, you might get zero for the article but if you’ve placed it in the right venue you may get a $15,000 or $20,000 speech out of that article. You might get a consulting contract. You might get access to opportunities that you couldn’t even have predicted.

You have to really open yourself up in the words of the internet theorist Doc Searls away from making money from something and understanding that nowadays you make money because of something and that’s a very different phenomenon.

Alison Jones: I’ve never heard it articulated so beautifully. That’s exactly it isn’t it. Content used to be the end and it’s now the means and it’s still massively important because you don’t get to your end without that means. But it isn’t the end in itself that it used to be.

Dorie Clark: That’s right. Yes.

Alison Jones: How do you think books fit into that picture?

Dorie Clark: Well, books are an interesting case and of course clearly I’m on your show talking about my books so I do believe in them in principle. These days there still is a cache with having written a book. In many cases, there’s sort of a thinking about that, okay, well, anyone can write a blog post or certainly anyone can write a Tweet. And so, do you have to have written a book? No, you don’t. If you have been a really consistent content creator in other ways over time. Nobody’s going to be really successful with one blog post but you know, if you’ve been blogging five or 10 years, yeah, you can build up a lot of cachet.

But a book is still viewed by many people, most notably conference organisers as the true test of your expertise. If you can write 200, 250 pages about something, then you know, by god, you must know something about it. That is, whether or not it’s true who knows.

Alison Jones: It’s quite a crude metric isn’t is?

Dorie Clark: Yes. But having a book is often what is necessary to start getting paid speaking engagements. If that is your goal, if that is something you want to do, then having a book is really valuable for that. Additionally, the other question of course that comes up is do you do traditional publishing or self publishing? All of my books have been traditionally published. This most recent one Entrepreneurial You is coming out from Harvard Business Review Press, which also published my first book, Reinventing You.

I do think that there is still a lingering cachet with having a traditional publisher although I think that that is steadily eroding over time. There certainly used to be a stigma attached with self publishing. There’s now no stigma attached to it. I think there’s a little benefit that comes from traditional publishing that may erode over time but certainly there’s nothing wrong with self publishing.

Alison Jones: Of course, it depends on the publisher as well doesn’t it? HBR, that’s a name to conjure with. Not all traditional publishers would have that brand behind it so yeah, you’re right about the cache there. I’m interested as well in the, I mean obviously that’s the quite a pragmatic reason to do a book. Then people will think, “Yes, she knows about her topic and they’ll book me to speak.” Tell me what else books do for you personally and professionally? I really want to get into what writing does for you under the hood.

Dorie Clark: Yes, of course. In terms of the writing process, I mean there really is a certain, I think it actually is relatively true that there’s a certain kind of mastery that comes from devoting that much energy to one topic. And so certainly for me as I’m rolling out Entrepreneurial You this is going to be the content that probably for the next couple of years I am primarily speaking about. It’s fueling me with a new range of anecdotes that I will be giving talks about, I’ll be blogging about, et cetera.

It’s kind of a way of periodically infusing yourself with fresh information. You don’t want to become a greatest hit record you know. You don’t want to be the band that just keeps playing your songs from 1965. You want to keep doing new things. And so writing a book is kind of an enforced discipline to do new research and to get new things to talk about.

Alison Jones: Yeah, that’s a very cool way of putting it actually. And do you do that quite strategically? Do you say, “Okay, over the next five years in my business this is the direction in which I want to go and here’s the book that’s going to be the engine of that,” or do you just go, “Huh, this is interesting,” and it all kind of flows from there?

Dorie Clark: Well, you know I was actually very strategic when it came to Entrepreneurial You and part of why I wanted to write it was that one of the things that I was hoping to do in my business was I had been interested in exploring the concept of doing online courses for quite a while. I realised, you know it’s kind of a complicated thing. I mean yes, anyone can theoretically slap up an online course but it’s probably not going to be very successful if you don’t know what you’re doing.

I thought, if I’m taking the time to do this, I want to do it right. I thought, “Well what would allow me to get access to a lot of really good information, high quality information about how to run an online course?” And I thought, “You know what, I could interview people. I could essentially write a book.” And so for me my secret agenda with writing Entrepreneurial You was that I wanted to have an excuse to “pick the brain” of all the really smart people that I knew that were monetizing in interesting ways so that I could basically have my really private coffee, ask them whatever I wanted and then the value that I would give back of course would be that I would share that information with other people and spread the word about their work.

But I made myself my first guinea pig for Entrepreneurial You and I really wanted to test whether these concepts work and so during the course of 2016, when I was writing the book, I was also simultaneously trying out new strategies that I had written about in the book. And so I did launch an online course, my recognised expert course and I put that out there. I did my first live workshop as a result of things that I learned in researching Entrepreneurial You and so I’m very proud to report that simply by applying the techniques that I had learned in the course of my research I was able to bring in nearly an additional two hundred thousand dollars in 2016 above and beyond what I had earned the year before. For me, I was able to really test and validate a lot of the ideas that I share in the book.

Alison Jones: That is a decent return on investment isn’t it?

Dorie Clark: Yes, absolutely.

Alison Jones: What I love about that, and I’m just beaming here because it just illustrates to beautifully, I have this model where the writing of the book is a sort of golden thread but the four areas that I’m looking at developing with my clients is developing themselves. The mastery as you were saying of the subject and the self-development. Developing the business, so building off the new product streams from it. Developing your network, and that example of this is a great excuse to find really smart people and pick their brains. Absolutely. Everybody loves being involved in a book. And building a platform. Just having interesting stuff to talk about, as you say, how ever many years it is. And you’ve just beautifully illustrated all of them so thank you. I couldn’t have asked for more.

Dorie Clark: Well, thank you. That’s great.

Alison Jones: I’m going to use that as a case study. That is awesome. And of course this is why I do the podcast is cause I get to talk to people like you and see examples of how it works in the real world, which is great.

Dorie Clark: Yes, even better.

Alison Jones: We are both evil geniuses aren’t we? Ah hah.

Dorie Clark: Ah hah, yes.

Alison Jones: What does writing look like though for you Dorie? Do you sit down at the crack of dawn with a smile on your face and pen 500 words and then meditate for a while? How does your routine go?

Dorie Clark: Definitely not. Definitely not at the crack of dawn. You know, one of the big mantras for me is I run my own business and so as a result writing has to fit into that business and so one of the things that I’m very passionate about is evangelising about the idea that you don’t have to have this sort of separate set aside time, like going off into a cabin in the woods, in order to write.

If you can have that, if you can take that, great, that sounds lovely. But for the vast majority of people it’s not practical to go rent a cabin for six months or a year and go write your master work. A lot of times people talk themselves out of doing the writing because they say, “Well, the cabin’s not possible so therefore the writing must not be possible.” That is patently untrue. I wrote all of my books while running my business. Did not take time off from it and was able to integrate it in. The way that I did that specifically was I … Typically I need a little bit of a chunk of time to write. It’s hard for me to do bookwork in a half an hour or an hour. It’s not like writing a blog post. I feel like I need to get in the zone because I need to orient myself to what I’ve written before and what I am going to write so that the pieces fit together properly.

But so during my writing periods I would carve out between three and four half days per week. Typically, this would three and a half or four hours and I would just mark it on the schedule. Let’s pretend it’s like a Monday, Wednesday, Friday morning. Let’s say nine to one, something like that. And so that would be my writing time and then I would do business, regular business the rest of the time. It was not an imposition on my schedule. I was able to accomplish it with a schedule like that for about let’s say somewhere between two and three months of building that time in I was able to get a very solid first draught of the book done. And so that’s how I powered through. For subsequent revisions I just fit it into my regular course of business.

Alison Jones: That’s awesome. And it’s so disciplined and so clear. It makes everybody listening go, “Yeah, I should probably do that. That sounds really sensible.” That’s so funny. I know exactly what you mean about needing a chunk of time because I’ve tried to do this micro habit thing and just spend half an hour and you do need time to think where you’ve been and where you’re going and by the time a half an hour’s gone you’re just about starting to produce something half decent and then you have to stop. Yeah, I think that’s really important. I actually had to take a weekend, well about three days, away from home just to finally nail my book, which I finally did a couple weeks back.

Dorie Clark: Nice.

Alison Jones: I know. But I was really struggling just to nail it from home. I kept farting around and it was something about the separation from where I normally sat. Which is pathetic. Yeah, it wasn’t quite a cabin but it was close. It actually did have a huge impact on the writing. I’m very interested in where people write and the impact of that. I think there’s a book in here somewhere. Yeah, maybe next time. When you’re sort of travelling do you manage to fit the writing around that as well or do you have to have your desk and your objects around you just so?

Dorie Clark: It’s a little hard to write while I’m travelling. Mostly because the, just your system is messed up. It’s like if you’re on a red eye flight or something like that, you’re overtired anyway. However, I try to schedule, if I’m working on a book I try to do it during periods where it’s not going to be a travel intensive period for me. That being said, I do a lot of shorter writing projects on planes and while I’m travelling.

All the time I was flying to, I’m trying to think of my previous stuff. Oh yeah, this is a good example. One of my writing projects, which in some ways it doesn’t sound like a writing project although it is, is I do these online courses for linda.com, which was bought by LinkedIn a couple years ago so they’re now in the process of rebranding it as LinkedIn Learning so these online courses. They have scripts for them and you as the creator have to write the scripts.

Typically, for a course there will be about 15 scripts and each one is roughly the length of a blog post. Maybe the welcome is just short but the main content ones are, let’s say between 500 and 700 words. It’s a substantial chunk of writing. And so I was flying back last week from Milan to New York and I, it was just this long nine hour flight and I’m like, “Wow, all right, this sucks but I’m not going to watch some stupid movie. I need to get something done.” This is a really busy period of for me. I took the nine hours and I wrote scripts for two courses. I just banged them out. It was the equivalent of close to 30 blog post-esque length things but over this nine hour period I just muscled through that sucker. I knew the material well so I was able to do it fast but yes, sometimes it’s just sheer force of will. But I can write when I’m travelling when I need to.

Alison Jones: I’m in awe. Every time I’m on a long flight I’m like, “I’m so going to use this productively,” and every time I end up with a crappy movie. I’m going to channel you next time I’m on a flight. Do you have it all planned out? I mean do you have a sense of, “Yes, this is the bit I need to write and these are the points I’m going to cover,” or do you just start writing and see where it goes?

Dorie Clark: Well, for the course for instance, it really was just a matter of execution because the previous phases of if, you know phase one is creating an outline and you already have that. They have to approve the outline in order to approve the course so I knew roughly what I was going to say. It was just kind of question of doing it.

Alison Jones: Does that translate to the books as well?

Dorie Clark: For the books I also have a pretty good idea of where I’m going with it. The way that I structure it particularly is, certainly for commercially published books of course you need to include in your proposal an outline of each chapter so you have that outline. And then the additional step for me, this kind of comes from my background as a journalist so if outlining is step one, step two is then doing the interviews so I have the content. Step three is, I’ll call it collating the interviews and so I basically go through, pull out the pieces of the interviews that I think are really interesting and salient and leave those quotes and those paragraphs.

Then I reshuffle them so that I’m I like, “Okay, this relates to podcasting so this should go in chapter six and this is for blah, blah, blah so this is chapter nine.” I just shove them into that place and so then when it’s time for writing I have both the outline in terms of the over arching script and I have the quotes and the pieces from the interviews that are there and so I have the raw materials at hand so I could just go and get started. Typically if I’m having a pretty good day, it’s not at all uncommon for me to about 3,000 words in a day.

Alison Jones: Yeah. That’s great. Basically you’re weaving the thing that’s going to hold it all together but essentially you know where you’re going and you’ve got the raw content in there so it’s just the stitching in. Yeah. Brilliant. That’s so interesting to find out how people do it. That’s really cool thank you. Now there’s people listening and they’re twitching through their first business book, what’s the one tip that you’d give them to help them?

Dorie Clark: Yeah, I think that, well one kind of easy thing that can just save time of course is to be willing to pay for a transcription service in case you are not a great typist. You can make it go a lot faster if you have somebody else do it. I use a service called Rev.com. R-E-V.

Alison Jones: It’s wonderful, yeah.

Dorie Clark: Yeah, super fast. A dollar per minute. That’s been a real life saver. Overall I think the question is, is it a book that you would want to read? I think sometimes we get thrown off because we just really want to write a book and so we can maybe concoct this thing in our heads, “Oh, someone would really like this, blah, blah, blah,” but I think the real question is, would you want to read it? Would you think this was interesting? Would you think this is new information? And if you would, then that’s a really good sign that it is something of value.

Alison Jones: It’s so true isn’t it because our attention is just under so much pressure. It’s so precious to us. It’s got to have a real reason for somebody to give it their attention. Not even just buy it. That’s a big commitment as well but it’s more about the attention. Am I going to ake some time out of my life to read this book? It’s a great question to ask yourself.

Dorie Clark: Totally, yes.

Alison Jones: Awesome. Now I always ask my guests who they would recommend as a guest on the show. Someone with something interesting to say about the business of business books. Who do you think would make a good guest for Extraordinary Business Book Club?

Dorie Clark: Well Alison, I’m going to recommend a woman named Mora Aarons-Mele who is the author of a new book called Hiding in the Bathroom. It is a book about introverts at work, which is a great topic and a great title.

Alison Jones: That’s a brilliant title.

Dorie Clark: Yes. She’s a Forbes contributor. Very interesting and talented. I think she’d be great for your audience.

Alison Jones: I’d love to know how she came up with the title as well. That’s awesome. Right, I shall ask her on. I don’t know her so thank you. I love it when I get a complete left field. I’ve never heard of her. Brilliant. Love to have her on. Now if people want to find out more about you Dorie where should they go?

Dorie Clark: Well thank you. I would steer people to my website, which is dorieclark.com and my new book is called Entrepreneurial You and in fact if people want to go deeper into this question about how to think more entrepreneurially and how to make more money then I would suggest that they might check out the free resource. It is an 88 question Entrepreneurial You self-assessment and they could get it at dorieclark.com/entrepreneur.

Alison Jones: Fabulous. And I’ll put that link up. Although I can’t imagine there’s anybody listening who wants to make more money so I’m not sure that’s going to go down well but we’ll see.

Dorie Clark: Yeah, you know.

Alison Jones: You know. Take it or leave it. Brilliant. I’ll put all those links up on the show notes so if you’re driving, if you haven’t got a pen and paper, don’t panic. Go and look at extraordinarybusinessbooks.com and it’ll all be there. And thank you so much for your time Dorie. Lisa was right. You were an absolute fabulous interviewee. Thank you.